Where to Go for a Long Weekend in 2019

When planning a trip for a long weekend, there's a lot to consider—you want to choose somewhere far enough where it feels like a true getaway, but close enough that you're not spending the entire weekend in transit. You want to go somewhere that offers plenty to do, but not so much that it feels you barely scratched the surface when you leave. With Memorial Day right around the corner, we rounded up the top destinations for a long weekend getaway this year, using a mix of editorial insight and data for our Editors' Choice Awards.

Craving a nature fix? Spend a day or two adventuring through Mt. Hood National Forest (outside of Portland) where you can hike, ski, and soak up the gorgeous scenery. Looking for a more artsy scene? Head to Hudson, New York (only two hours from the Big Apple) to browse art galleries, antique shops, and boutique stores. These, plus the other top picks below, are the ideal long weekend getaway—they're nearby major cities making for convenient travel and they're packed with plenty of activities and sights to fill a 72-hour itinerary.

Use this list to plan your long weekend getaways this year, whether that's for Memorial Day, Labor Day, or any other time you are able to tack on one more day to your usual Saturday and Sunday.

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Key West, Florida

Duval street, Key West, Florida, USA.

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Address
Key West, FL 33040, USA

When in Florida, a road trip anywhere outside the state can be an ordeal, so why not head to the Southernmost Point instead (from Miami, it’s about a three-hour drive). Stay at the Perry Hotel in Stock Island — a peaceful, dog-friendly respite far enough away from the noisy crowds of downtown, but also a quick drive from the famed Duval Street. Take a tour of the Hemingway Home and then go have a drink at the Green Parrot Bar, a Hemingway favorite built in the 1800s. In Mallory Square, you’ll find a daily Sunset Celebration, complete with fire-breathers, psychics and other quirky street performers. Right next door, grab a bite and a mojito at El Meson de Pepe, a Cuban eatery that boasts the only live Cuban band on the island. And of course, set aside some time for watersports. Whether it’s boating or jet-skiing, swimming or snorkeling, some of Key West’s most marvelous treasures are found on — and under — the surface of the sea. —Allison Ramirez

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Mt. Hood, Oregon

Mt Hood, Mountain, Lake, Sunrise - Dawn, Trillium Lake

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Address
Mt Hood, Oregon 97041, USA

While you’re in Portland, don’t just gaze at Mt. Hood looming to the east — get up to the mountain yourself. Not only does it boast the country’s longest ski season, it also offers countless hikes, pristine alpine lakes, and staggering views of the Cascades. Stay at The Timberline Lodge, a gorgeously preserved 1936 landmark perched at the mountain’s tree line. Its exterior was famously used for the horror flick “The Shining,” but inside it’s all cozy vibes and rustic charm. Eat at one of Timberline’s restaurants, or grab a local brew and steelhead chowder at Mt. Hood Brewing Company in nearby Government Camp. Take the scenic route, where you’ll drive alongside the majestic Columbia River Gorge with stops like Multnomah Falls (Oregon’s largest waterfall at over 600 feet), then through the picturesque orchards and vineyards of Hood River before winding your way up the mountain. —Elizabeth Brownfield

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Tupelo, Mississippi

Tupelo, Mississippi

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Address
Tupelo, MS, USA

The King of Rock 'n' Roll was born in Tupelo, thus any trip to this Mississippi city ought to start with a visit to the Elvis Presley's birthplace. Meanwhile, the city's charming downtown is home to Tupelo Hardware Company, where Elvis got his first guitar, and true fans can eat at Johnnie’s Drive-In, where the King was known to enjoy a burger. But Tupelo is more than just Elvis Presley: Nestled in the scenic hills of Mississippi, the town offers easy access to the scenic Natchez Trace Parkway, a historic 444-mile road managed by the National Park Service. Connie’s Fried Chicken serves road-trip-worthy blueberry doughnuts — even the local Blue Canoe restaurant uses them in their bread pudding dessert. When you need to rest, the Hilton Garden Inn is a convenient family-friendly option; for a more rural experience, head to Moon Lake Farm B&B, which offers on-site fishing and horseback riding. —Margaret Littman

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San Marcos, Texas

Hopkins Street facing courthouse square in historic downtown San Marcos, Texas, USA

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Address
San Marcos, TX, USA

Texans and non-Texans alike may know San Marcos as the home of Texas State University and two rather popular outlet malls, but this quaint, charming town is so much more than Bobcats and affordable fashion brands. Flanked by towering cypress trees, the spring-fed San Marcos River flows directly through downtown; climb into an inner tube and let the gentle breeze take you away. Nature lovers should also check out Purgatory Creek Natural Area, which is home to over nine miles of trails that wind through lush meadows, stunning canyon bluffs, and dense clusters of oaks. Fuel up at Industry, a stylish, open-air café on the square; if you’re thirsty, a trip to AquaBrew Brewery & Beer Garden is in order. At the end of your day, check into the Crystal River Inn for an intimate-yet-upscale B&B experience. —Justine Harrington

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Ojai, California

Views of the Ojai Valley and Citrus Trees from Ojai, California

 

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Address
Ojai, CA 93023, USA

Although only a two-hour drive from LA, this foothills town outside Ventura feels worlds away from the urban sprawl and never-ending hopscotch game that is life in the big city. Thanks to the massive oaks, citrus groves, surrounding Topatopa Mountains, and vibrant sunsets that result in the spectacle locally known as the “pink moment,” it’s got bucolic splendor to spare, much of which can be hiked, biked, climbed, or explored on a Cloud Climber Jeep tour (Meditation Mount, Ojai Valley Land Conservancy). It’s home to as many farmers as crystal-toting bohemians, artists, winemakers, and makers crafting candles, dreamcatchers, craft beer, jewelry, beard oil, and kombucha. The mixed population results in an amazing array of shops, galleries, yoga studios, wellness providers, and tasting rooms in the very walkable downtown. It’s small enough that the world’s largest open-air bookstore (Bart’s) can still operate on the honor system but large enough to host storytelling, art, music, and lavender festivals. Many restaurants (Azu, Knead Baking Company, The Farmer and The Cook) plan menus around local products (Ojai Olive Oil, honey) and produce, especially in the spring when the rare Ojai Pixie is harvested. There’s almost as much variety in accommodation options. Glamp in Instagram-friendly Airstreams (Caravan Outpost), get cozy at a converted schoolhouse turned B&B (Lavender Inn), or splurge on all the bells and whistles like spa treatments and beekeeping experiences at a historic Five-Diamond (Ojai Valley Inn). —Carrie Bell

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Prince Edward County, Ontario, Canada

 

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Address
Prince Edward, ON, Canada

Prince Edward County checks all the boxes for a relaxing weekend at the lake, including the ones you didn’t even know you were looking to fill. Situated on the northeastern shore of Lake Ontario, the water is an obvious draw: with three sandy beaches, considered some of the best in all of Canada, and the world’s largest baymouth barrier dune formation, Sandbanks Provincial Park is where you’ll want to spend your warm, sunny days. The shallow waters of Outlet Beach are perfect for families, while Dunes Beach, named for its towering pale sands, offers the most dramatic scenery. From the hip Drake Devonshire resort to private cottage rentals, there are lots of places to get your cabin on, and no shortage of County-grown or made goodies to stock in your kitchen for the perfect summer grill night. Hit Agrarian Market for local meats, dairy and bread, Vicki’s Veggies for fresh, seasonal produce, and — a key draw to the region — more than 40 wineries, breweries and cideries to keep your thirst quenched. —Alyssa Schwartz

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Athens, Georgia

 

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Address
Athens, GA, USA

Home of the University of Georgia’s flagship campus, Athens is just an hour’s drive from Atlanta and a top destination for music and food lovers alike. Stay at the historic Graduate Hotel in the heart of downtown and start your trip by sampling top-rated local beers at Creature Comforts and Terrapin breweries. Then dine on seasonal, Southern fare at celebrity chef Hugh Acheson’s celebrated Five and Ten restaurant and cap your evening with live music from at venues 40 Watt and the Georgia Theatre, where homegrown bands R.E.M. and Widespread Panic got their start. —Laura Scholz

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Boulder, Colorado

Pearl Street Mall, Downtown Boulder

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Address
Boulder, CO, USA

Located about 40 minutes outside of Denver, Boulder is a convenient and ideal day trip or long weekend getaway from the Mile High City. This college town offers a taste of the best Colorado has to offer. Boulder is home to more than 20 breweries (Avery is a popular option and a 2018 Editors’ Choice winner), and it’s the perfect place to base yourself for outdoor activity, including hiking through the scenic Chautauqua Park at the base of the Flatirons, rock climbing at Boulder Canyon, spending a day on the water at Boulder Reservoir, and more. At night, stroll through downtown’s Pearl Street, a pedestrian street lined with bars, restaurants, shops, and of course, more breweries. —Jamie Hergenrader

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Valle de Bravo, Mexico

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Address
Valle de Bravo, State of Mexico, Mexico

A two-hour drive west from Mexico City will bring you to the charming town of Valle de Bravo. With a pleasant main square, colonial period church, and picturesque lake that’s the setting for water sports such as sailing, water skiing and paddleboarding, it’s an ideal destination for a weekend retreat from the big city. The town is ringed by wooded mountains brimming with opportunities for adventure, including hiking, biking, rock climbing, and hang gliding. When you’re ready for more tranquil pastimes, stroll cobblestone streets, shop for handicrafts, or visit the small archaeology museum. For a fun and memorable dining experience, head to Los Pericos, a floating restaurant popular with Mexican families that offers great seafood and even better views. After a full day of activities, Hotel Rodavento provides peaceful luxury with cabins set in the forest around a small private lake. Achieve maximum relaxation with a treatment at the hotel’s full service spa, the perfect cap to an exciting and restful getaway. —Suzanne Barbezat

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Hudson, New York

The Wick Hotel

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Address
Hudson, NY 12534, USA

Located on the east side of the Hudson River, a little more than two hours from New York City, is Hudson, a haven for artists, chefs, and outdoor enthusiasts. The venues themselves look like art. The Wick, a year-old boutique hotel, is located in a former candle factory and has blueprints of equipment on its walls. And in the back of one of the many antique stores, you'll find Backbar, a cocktail bar in a garage covered in neon, sparkling lights. While this little city itself has a lot to do, don’t forget to spend time hiking or biking in the surrounding rolling mountains. —Alyson Krueger

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Indianapolis

Skyline Indianapolis

 

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Address
Indianapolis, IN, USA

While historically known as a sports town, Indianapolis has been refining its reputation as a culinary and cultural destination for years. Popular neighborhoods include White River State Park, Fountain Square, Broad Ripple Village, and Mass Avenue. See the sights at Newfields, a 52-acre complex known for its gardens and home to the Indianapolis Museum of Art. For a day dedicated to the kiddos, the Children’s Museum of Indianapolis is the world’s largest. Book downtown digs at The Alexander, a Dolce Hotel, which combines contemporary design with a convenient location. Foodies will fall in love with Bluebeard, a James Beard Award semi-finalist dedicated to inventive cocktails and cultivating relationships with local farmers. Round out your 72 hours in Indy with brunch at Milktooth. While it has earned a reputation as one of the best spots in town, it hasn’t gotten too big for its britches. —Courtney Kellar

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Madeline Island, Wisconsin

View of the Bay, Lagoon Ridge Trail, Big Bay State Park, Madeline Island

 

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Address
Madeline Island, Wisconsin, USA

Madeline Island is the largest of the Apostle Islands, a set of 22 islands famous for their rocky sea caves. Get an early start at Bayfield's Old Rittenhouse Inn and enjoy a gourmet two-course breakfast. Then take a short ferry ride to one of the Midwest’s best hidden treasures. Kayak through the sea caves, rent bikes, or book a cruise around the neighboring islands, where you'll learn about the history of the Apostle Islands and how important they were in Native American culture. After exploring, relax and have a drink at Tom’s Burned Down Cafe, a charming outdoor bar where you can find live music and quirky local personalities. —Taylor McIntyre

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The Best Destinations for a Long Weekend in 2019